1.0 2011-09-21 00:11:18 UTC 2015-07-21 06:57:07 UTC FDB022271 Neuraminic acid Neuraminic acids are the commonest sialic acids in nature. Most sialic acids on gangliosides share a core neuraminic acid (Neu) structure and are N-acylated at the C-5 position with either an N-acetyl or an N-glycolyl group (giving Neu5Ac or Neu5Gc, respectively). It was originally thought that unsubstituted glycosidically linked Neu did not occur in nature. However, there have been several reports suggesting its presence in gangliosides and more recently in mucin-type glycoproteins. The N- or O-substituted derivatives of neuraminic acid are collectively known as sialic acids, the predominant one being N-acetylneuraminic acid. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: acetyl, lactyl, methyl, sulfate and phosphate groups have been found. Sialic acids are found widely distributed in animal tissues. Sialic acid rich glycoproteins bind selectin in humans and other organisms. Cancer cells that can metastasize often have a lot of sialic acid rich glycoproteins. This helps these late stage cancer cells enter the blood stream. (PMID: 11884388) [HMDB] 5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonate 5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acid Neuraminate O-sialate C9H17NO8 267.2332 267.095416525 (2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid β-neuraminic acid 114-04-5 N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O InChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1 CERZMXAJYMMUDR-YOQZMRDMSA-N belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Acyl carnitines Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Amines Carbonyl compounds Carboxylic acid esters Carboxylic acid salts Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organic salts Organopnictogen compounds Tetraalkylammonium salts Acyl-carnitine Aliphatic acyclic compound Amine Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Carboxylic acid salt Dicarboxylic acid or derivatives Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organonitrogen compound Organooxygen compound Organopnictogen compound Quaternary ammonium salt Tetraalkylammonium salt Fatty acyl carnitines O-acyl-L-carnitine O-propanoylcarnitine Solid logp -3.30 ALOGPS logs -0.02 ALOGPS solubility 2.55e+02 g/l ALOGPS logp -5.6 ChemAxon pka_strongest_acidic 2.72 ChemAxon pka_strongest_basic 8.25 ChemAxon iupac (2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid ChemAxon average_mass 267.2332 ChemAxon mono_mass 267.095416525 ChemAxon smiles N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O ChemAxon formula C9H17NO8 ChemAxon inchi InChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1 ChemAxon inchikey CERZMXAJYMMUDR-YOQZMRDMSA-N ChemAxon polar_surface_area 173.7 ChemAxon refractivity 54.34 ChemAxon polarizability 23.67 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 12849 Specdb::CMs 37792 Specdb::CMs 131424 Specdb::CMs 139158 Specdb::CMs 1077719 Specdb::CMs 1077721 Specdb::CMs 1077722 Specdb::CMs 1077724 Specdb::CMs 1077726 Specdb::CMs 1077728 Specdb::CMs 1077730 Specdb::CMs 1077732 Specdb::CMs 1077734 Specdb::CMs 1077736 Specdb::CMs 1077738 Specdb::CMs 1077740 Specdb::CMs 1077742 Specdb::CMs 1077744 Specdb::CMs 1077745 Specdb::CMs 1077747 Specdb::CMs 1077749 Specdb::CMs 1077750 Specdb::CMs 1077752 Specdb::CMs 1077754 Specdb::CMs 1077756 Specdb::MsMs 46845 Specdb::MsMs 46846 Specdb::MsMs 46847 Specdb::MsMs 153195 Specdb::MsMs 153196 Specdb::MsMs 153197 Specdb::MsMs 2394511 Specdb::MsMs 2394512 Specdb::MsMs 2394513 Specdb::MsMs 2571911 Specdb::MsMs 2571912 Specdb::MsMs 2571913 HMDB00830 27851 #<Reference:0x000055ce324e61e0> #<Reference:0x000055ce324e6028> #<Reference:0x000055ce324e5e70> #<Reference:0x000055ce324e5cb8> #<Reference:0x000055ce324e5b00> #<Reference:0x000055ce324e5920> #<Reference:0x000055ce324e5768> #<Reference:0x000055ce324e5588> #<Reference:0x000055ce324e5380> #<Reference:0x000055ce324e51a0> #<Reference:0x000055ce324e4f98> #<Reference:0x000055ce324e4d90> #<Reference:0x000055ce324e4bb0> #<Reference:0x000055ce324e48b8> #<Reference:0x000055ce324e46d8> #<Reference:0x000055ce324e44d0> #<Reference:0x000055ce324e42f0> #<Reference:0x000055ce324e40e8> #<Reference:0x000055ce324ffed8> #<Reference:0x000055ce324ffd20> #<Reference:0x000055ce324ffb68> Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase Q9Y223 GNE